Phosphorus pentachloride → (4-Fluoro-3-phenoxyphenyl)methanesulfonyl chloride

HRID 479886Notes

Reaction equation

HRID 479886 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([O-])(=[O:11])=[O:10])=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:22]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([Cl:22])(=[O:11])=[O:10])=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 86757418Sodium (4-fluoro-3-phenoxyphenyl)methanesulfonate

Product 1

HCID 18000351(4-Fluoro-3-phenoxyphenyl)methanesulfonyl chloride

Procedure

The sodium sulfonate obtained in step 1 is mixed with phosphorous pentachloride at room temperature for two days. An ice-water mixture is added and the aqueous solution is extracted with methylene chloride. The organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain (4-fluoro-3-phenoxyphenyl)methanesulfonyl chloride as a syrup (2.05 g).

Workup

  1. extractionthe aqueous solution is extracted with methylene chloride
  2. extractionThe organic extract
  3. washis washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06dc0694242f41569ec45c17784ef03d
Source dataset
uspto-grants-2003_11
Patent number
US06646166B1

Reaction notes

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